Simonton Court Hotel Key West

Hotel · Key West

Simonton Court Hotel Key West

Hotel · Key West

1

320 Simonton St, Key West, FL 33040

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Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null
Simonton Court Hotel Key West by null

Highlights

Historic property with gardens, pools, and free breakfast  

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320 Simonton St, Key West, FL 33040 Get directions

simontoncourt.com
@simontoncourt_keywest

Information

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320 Simonton St, Key West, FL 33040 Get directions

+1 305 294 6386
simontoncourt.com
@simontoncourt_keywest

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wifi

Last updated

Aug 13, 2025

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The Best Hotels in Key West of 2024

"Simonton Court Historic Inn & Cottages offers up a taste of Key West in the island’s Old Florida style. If you’re looking for a cute and quaint bed and breakfast, this is your frontrunner. Here, 30 rooms are spread out across 10 buildings on five properties, including a set of historic cottages built in 1880, giving guests an intimate and secluded feel right in the center of bustling Old Town." - Travel + Leisure Editors

https://www.travelandleisure.com/best-hotels-in-key-west-8629263
View Postcard for Simonton Court Hotel Key West

Mj mg

Google
They care about their guests! I cannot say enough about this gorgeous bed and breakfast. It's very private and romantic with cozy rooms and guest cottages. But more importantly, the staff members are so kind and accommodating. Even before I arrived there was a mix-up with the parking and they found a solution right away! HIGHLY recommend!!!!

sherrig296

Google
I can’t say enough about my stay here. It was awesome!! Room so comfortable and the bed amazing. I didn’t want to get up from bed. Also but especially give a shout out to the amazing wonderful individuals who gave us such care. Violet who worked the daily breakfast and her husband Jonathan were so wonderful to us as we celebrated our 1st year anniversary and my birthday. They went above and beyond to make our stay memorable. I would definitely recommend anyone who comes here to visit !!

Ed Wetzel

Google
Simonton Court is the place that hooked us on visiting Key West twice a year. All of the rooms are different, which make each stay a different experience. We’ve stayed in both the cottages and the mansion. We love the history of the complex and the classic Key West vibe. Walking down “Hurricane Alley” is too cool with all of the cute little cottages. The location is perfect, close enough to walk to everything, but far enough from the hubbub of Duvall. There are four pools, each with their own character that are accessible 24/7. The continental breakfasts are nice, and we like the complimentary iced tea and coffee available at the pool gazebo throughout the day. On the downside, some of the rooms and baths can use a little updating. Only once did we have a problem with noise. We had the misfortune to be next to some party animals who carried on throughout the night. Otherwise, our stays here have been pleasurable.

Jordan Upchurch

Google
Such an adorable spot hidden in Key West! This historical property offers an array of different room types. It also has four pools, free breakfast, and adult beverages during Happy Hour! Plus it’s super close to Duval Street, where there are over 100 bars and restaurants! The staff was so kind and constantly checked in to make sure that our stay was perfect! We highly recommend one of the cottages as you feel like you’ve rented your own home!

Christopher Bridge

Google
We absolutely loved our stay at Simonton Court in Key West! Our room was adorable and cozy, with a super comfortable bed that made it hard to get up in the mornings. The entire property is beautifully maintained, with four unique pools tucked among lush tropical gardens—it truly felt like a hidden paradise. The location is perfect, just a block from Duval Street, so we were close to all the action yet felt like we were in our own quiet oasis. On-site parking made everything even easier. The staff was outstanding. My wife had wonderful conversations with Violet and her husband Jonathan—both were incredibly kind, welcoming, and helpful throughout our stay. A simple but very cool breakfast was included and added a nice touch to start each morning. We’re already looking forward to coming back and exploring some of their other rooms. Highly recommend this gem in the heart of Key West!

kevinsN2638XX

Google
10/10. I booked last September for a 3-night stay after reading so many great reviews. The staff were extremely helpful, friendly, and accommodating. I thought it was a nice touch that they texted me a couple of times over the first day to make sure my room met expectations and if there was anything they could do to make my stay more enjoyable. Jonathan, Heather, and Laura were outstanding! The grounds were amazing and had you feeling like you were in a private resort. The room (TH3) and private deck were very nice and clean. As a solo traveler, it was ample space. This specific room might have been a bit cluttered if traveling with a companion, however. Important to me was how quiet it was. I never heard a thing in my room and you are a couple blocks from Duval St - ~5 min walk. I thought it was also nice that they provided breakfast service on the main patio and offered a choice of a complimentary beverage while staying there. Overall, a perfect "landing base" to come back to after being out all day. I have been in Key West many times but never downtown. I will likely not stay anywhere else when returning. Keep up the great work - you guys have figured out how to provide a pampered experience!

Bill Verschuren

Google
My wife and I spent the weekend at the Simonton Court and really enjoyed our stay. The grounds are wonderfully kept, full of palm trees, ferns, and gorgeous orchids. There are several small pools and a common area with patio tables & chairs, which is where breakfast is served each morning. Breakfast is ok, they have good coffee already made but breakfast does not start until 8:30 am and don't expect an omelette. There is no kitchen! They offer flavored yogurt, toast, English muffins, cold cereal, granola, and bagels. Their French toast and waffle is the frozen kind already made, which they warm up in a toaster. The best they had to offer were the bagels and hard boiled eggs.The employees were kind and friendly, which made our stay more enjoyable. The hotel had a fun happy hour on Saturday afternoon that included coconuts painting, which we really enjoyed. The facility was not fully booked, but we made our reservation through Expedia and I believe that we got less privileges than guests who reserved a room directly with Simonton Court (such as check out time at noon vs 11:00 am). Additionally, we were assigned room MA5, which is in the mansion's third level. Keep in mind that there is no elevator, so you have to go up the three levels each time one needs something from your room. The room was comfortable enough, the shower needed some grout cleaning, and the hotel should consider upgrading their TVs. It also would have been nice to stay in one of the lower level rooms in the mansion, which had a little front porch. One of those rooms was empty during our stay. Overall, we enjoyed the Simonton Court and will book it again (but this time directly through the hotel).

959cassidya

Google
Where do I begin!? First, the staff at Simonton Court are wonderful - they are caring, kind, and so accommodating to all guests. Specifically, Jonathan and Violet really went out of their way to make our baby moon the most memorable trip! Second, the hotel itself is so beautiful! We loved the tranquil setting, the pools, and the lush greenery. Third, the breakfast is fantastic! It was so peaceful to come to the beautiful poolside patio every morning to eat a big breakfast. I would HIGHLY recommend Simonton Court to anyone traveling to Key West for the most peaceful and relaxing stay:-)
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Rachelle G.

Yelp
Best place to stay in Key West! My husband and I have stayed at Simonton Court over a dozen times and each and every time we fall back in love. Perfect for a getaway for two or a group of friends! All of the cottages are wonderful and feel like 'home'. The property itself is GORGEOUS! From the orchids to the cats roaming the property. Best part, the staff is wonderful. Very kind. Very helpful. Very Welcoming!

A S.

Yelp
What an amazing place to stay..it has soo much charm..we stayed in Cottage 1..it was perfect..well decorated..clean..our beds were comfortable the landscape is lush and gorgeous ..loved the rockers and swing on our cottage porch..in the evening they light these Lil lanterns on the tables by the pool area and also on the cottage porches talk about serene. The peaceful vibe this place has is undeniable!!! Complimentary coffee tea all day...breakfast was pastries ..bagels fruit waffles etc...and last but not least the staff..they were soo friendly,respectful and we appreciated them and the way they made us all feel welcomed!!!

Jim S.

Yelp
The place was great and in the middle of everything. The staff were amazing, friendly, and helpful. Jonathan was the BEST and his wife was so nice as well. Those two made our stay the best. We had MH1 and MH2 which basically had a private pool. We had 4 couples and spent our afternoons and evening at the pool. Perfect size for cooling off. MH1 got a little warm during the afternoon between 4pm and 7pm with the high ceilings but cooled down by the time we returned from dinner. The grounds were kept up and had a secured gate after 6pm. Thanks for making this trip a great one!!
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Ginamarie P.

Yelp
Great place to stay close to all the action. Clean and very charming ! Eric was very hospitable
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Kiarra S.

Yelp
Booked this hotel last minute and boyyyy she did not disappoint. The staff was super friendly, landscaping but beautifully manicured. They have 4 pools, multiple bungalows and hotel rooms. They offer a continental breakfast in the morning that has bagels, muffins and fresh brewed iced tea. Our room was spotless, super cozy and even had a little balcony looking out over the landscaping. We didn't really hear our neighbors at all, which is a big plus. It's centrally located to Duval and a lot of other great places. I wish we had more time to stay there but we'll definitely be back! Plus resident kitties that are so cute and friendly.
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Emily W.

Yelp
We've been visiting KW for 20+ years and have stayed in several different places. I booked a last minute trip and all my favorite haunts weren't available. I took a chance and tried something new (to me) and was just thrilled with the people, the property, the accommodations, and the amenities. Everyone was friendly, my room was spotless and well appointed (Key West Aloe products? Score!), and you're steps from all the best places. I already had my next trip to KW planned but I think I'll be moving my lodging reservation over to Simonton Court!
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Dayna K.

Yelp
I loved this property - Key west lodging can be a gamble- either really good or really bad ...... this place was fantastic . The room we were in was comfy - cozy and clean . ( C7a- we loved the hammock) The grounds of the property was beautiful and the location is very close to Duval street. The staff was really friendly. Personable !! I will stay here again . Hint - book directly thru the property. They price match and you get so much more amenities than using a 3rd party provider )
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Marqus R.

Yelp
Just off the beaten path but located right in the heart of everything that makes Key West, the distinct Key West culture that it is, Simonton Court Historic Inn & Cottages is a Yelp Five Star for me. It covers some 2 acres with elegant and fastidiously redone and redesigned historic homes. You even have distinct choices of places to stay within Simonton Court. There is the Mansion (my favorite), Comprised of 6 rooms in a traditional Bahamian style mansion house. Then you have about seven separate Key West cottages, formerly homes of cigar workers. Then there are about nine rooms in their Historic Inn with each room different. There is also the Manor House, originally of shotgun house design, with two rooms facing its own pool, and their most elegant Townhouse also with a pool of its own. In all, Simonton Court just can't be beat no matter where you choose to room. The service I had at Simonton Court was top-notch, exceptionally professional, and totally caring and polite. And yes, Simonton Court also has concierge services with breakfast included. When I checked in, the manager was Steven, one of the most pleasant and helpful rooming managers I've ever come across with a true understanding of what hospitality means.

Meghan S.

Yelp
Wonderful service! Steps off of Duval. Complimentary reusable water bottle and water stations throughout. Amazing!!!
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Shawnda L.

Yelp
We stayed at Simonton back in July to celebrate my boyfriend's bday and it was wonderful. Location is great. They were doing construction right outside the hotel on the street so it was a little difficult to find the day we arrived but we got there. The staff was wonderful so helpful and friendly. The room was nice, it's not modern but it was clean, comfy and had everything we needed. We stayed in Manir House 1 and I will certainly stay here again. Full kitchen! The cool thing about Simonton Court is you have options. They have 2 Manor Houses that share a pool so almost seem like your own private pool. Then they have townhouses that share their own pool, cottages which some have their own pools and then rooms in the mansion which is has a large pool. We absolutely loved hanging out by the pool, we even had a free lizard show. Tons of lizards and iguanas. They don't bother you and they keep their distance. Only reason not 5 stars was the free breakfast. It was cold bagels and maybe yogurt. With COVID I can understand they have to be careful, I would have liked to see a little nicer presentation and maybe more options. But certainly not a dealbreaker plus KW had some fantastic breakfast spots. SUGGESTIONS; - Reserve a parking spot. You will thank me later. Parking is a beast in KY - Room choices can be overwhelming, call and speak to someone at hotel they were very helpful. - Look into renting and reserving a golf cart or bikes. They go fast and you can get a pretty good deal for multiple days.
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Johnye V.

Yelp
What a fabulous stay in the heart of Key West! My husband and I stayed here for our honeymoon, and arrived exhausted after a red eye flight and a completely sleepless night. Staff were super welcoming and able to check us into our room well before the technical check in time, which was amazing considering all we wanted to do was lay in a bed! The grounds are absolutely beautiful, lush with greenery, and multiple cottages, allowing a very private feel that was so different from any hotel property I've ever stayed at. They have resident cats on the property too! Alvin was my dude, always chilling at your feet. They have multiple pools available for all guests to use as well. We were lucky enough to get one of the cottages and absolutely loved it! It had all the comforts and coziness of being in your own home, with touches of vintage charms in an upgraded modern vibe. There's a complementary breakfast with a small bar available on property. It's centrally located to Duval street, so we were able to walk everywhere! Don't even rent a car. Get an Uber into the city and enjoy your time walking or biking around. If I ever find myself back in Key West, we'll definitely be staying here again!
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Melissa M.

Yelp
This is an old cigar factory that has cottages and rooms. The two bedroom cottages were used by workers at the factory. The whole place is charming and has lovely gardens, brick pathways and three pools. I felt safe because the hotel had a coded entrance. There was a lovely patio where complimentary breakfast was served. This was also open in the afternoons for happy hour. The staff was very cordial and efficient. The hotel has little or no parking, but it is situated downtown within walking distance of restaurants, bars, and shops. The pictures of the rooms were very nice. The rooms have a fridge, coffee service, and a safe. The plumbing worked but not modern (toilet wouldn't flush on its own) and the lighting consisted of two little bedside lamps and two scones in the bathroom. The balcony had two chairs but that pretty much filled the balcony. The view was of part of the pool and the roof. However, my room was located on the third floor of the mansion. There was no elevator!!! I am a 69 year old woman. After three days in an attic room with no insulation, I felt like I was better organized and healthier. There was no way that I was running up and down those stairs several times a day. Thankfully, I work out four days a week. Otherwise, I would have needed oxygen and a defibrillator or a paramedic. I guess that a three floor walk up with exposed pipes that cost as much as a five star hotel room is expected in Key West. I never realized how grateful a 69 year old woman would be not to have to carry a large suitcase up and down three flights of stairs. Be sure to rent an electric car, not a golf cart and be sure that you check out the seatbelts to be sure that they do not give way as you turn a corner or if you hit a bump. Consider this sage advise.
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Molly E.

Yelp
Such a great way to relax in January away from the snow! Staff is friendly and very helpful! Close to walk everywhere so you don't even need a car. The courtyard is the beautiful, from breakfast, to lounging by the pool, to happy hour! At night it is perfect with all the lighting. It's very well done! Each room is different so we will be coming back every year to stay in a each one. I should say something negative so people don't find out about this place. Oh yes, the rooster waking me. That's it. (Even tho they are all over the island and you can't get away from them) Make sure to partake in one of their hosted events too. All are fun! I have to say again that the staff is wonderful. I can't say enough about great customer service since it seems to be a lost art form at times. When it does happen they should be appreciated. So THANK YOU very much! We will for sure be back. Oh wait. It's already booked!

Peter P.

Yelp
Without warning they canceled my reservation a week before our trip. Terrible business practice during high season. They suck!
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Joel R.

Yelp
Great place with a great location. My wife and i did 3 nights here and absolutely love it. Location is one block East of Duval St n the mid-northern end. Perfect for landing in the middle of the shops. Everything has been a short walk away. The room we had (SC5) is small but if you spend all day in the room you're either doing it wrong or only concerned with the bed . The room is clean and mostly well kept. The place isn't new but the imperfections are minor and add to the charm. Outside there are 4 pools with 24 hour access. It was chilly on our stay and, regrettably, we didn't put a tow in the pool until our last night to realize they are very heated. We took a dip and enjoyed it. Breakfast is a traditional continental that is ordered and delivered to your outdoor table by the main pool. It was basic but good. The grounds are quaint and have an intimate feel. The landscape makes for narrow paths to traverse the property front to back making you feel as if it's all private. Our room was close to Simonton St which we could hear an occasional motorcycle or EMS go by, no biggy. Staff was very friendly had helpful. No complaints here. Summary: Nice smaller rooms 4-warm pools Phenomenal location Included breakfast Beautiful landscape throughout.

Sarah D.

Yelp
Just stayed here with my family. It is actually even prettier than you see online. All employees were super-nice from the front desk, the lady that helps with painting on Friday night, the breakfast staff, the maids. The rooms were spotless. The grounds are so, so beautiful. Love the artwork throughout, so warm and inviting. Very beautiful and love the pools! We stayed in a cottage and it was beautiful. Well-maintained.

mark t.

Yelp
I booked 2 rooms for two nights , paid more than $ 500 per night per room. First room was on the third floor no elevator ( very high stores ) with stiff stair case . This room has big bims above the head And I hit my head several times. Also the room did not have a telephone set and I couldn't Rich the front desk , T. V. set did not work at all, shower cabin has some mildew in the corners, First morning I was waiting to 45 minutes for just for toaster bagel ( they lost my order). The second room was on the very high second floor with no elevator as well (This rooms have been given to us -75 years old guests???) The showehead hose have been leaking crating a mess Around a bathtub Doorlock have not been working properly and we had troubles to open the door. Our vacation have been ruined. The hotel/Expedia Shall pay me back the many for this entire stay in this hotel The property manager Sofia have been informed and promised to contact me with a resolution I did not receive any response . Regards, Mark My phone 5107898493
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Meghan H.

Yelp
Just spent 3 nights before Christmas there celebrating my mother's birthday. Gorgeous!!! Beautifully decorated and the staff was incredibly nice! The grounds were amazing and I would highly recommend!!

Ramon N.

Yelp
I cannot say enough great things about this place. It's beautiful, it's quiet, it's relaxing, and it's centrally located to everything you want to be able to walk (or stumble) back to the hotel from. I've stayed many times and it's a must for everyone.
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Feather F.

Yelp
Absolutely best hotel I've ever stayed in key west ! Been coming to key west 20 years & I will book this 100% when I visit . Amazing rooms , private balconies , friendly staff multiple pool areas & you can't beat the location. We had stayed once before & they left us a welcome back card & a little gift ! I can't wait to come back just to stay here again !!
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Robert H.

Yelp
We stayed here for a bachelor party and booked it at the suggestion of a friend thats from the area. I've been to Key West 4 times and this is by far the most comfortable place I've stayed in yet in Key West. We were in cottage 2. It's very cozy and quiet and it's nice to walk right out your door and be at a pool. You can be as private as you want or hang out on a porch or by the pool. The room was clean and very nice. It was very spacious for 4 people in a room. Yes the price is high here, but after having stayed at 2 other places in the area I am very happy with my experience. The WiFi was pretty weak. My only disappointment was that I expected a nice breakfast and it was just a glorified continental breakfast. I debated between giving it a 4 or 5 star and decided on a 4. Will happily stay here again!
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Lisa P.

Yelp
Stayed the last night of Fantasy Fest. The best location ever !! Eric and Jeniece were so nice and hospitable. You need to have this little gem in your life . Beautiful grounds. 30 different rooms. Stayed in C6B. I think that was it. Loved the room. Lots of room , private little space to have coffee outside in the morning. Very close to the rear pool. Make this your first call for a reservation. You won't be disappointed!

Jessie T.

Yelp
My husband and I stayed here for our honeymoon and we absolutely loved it. We stayed in room MA6 and really enjoyed our rooftop patio as well as private jacuzzi. The property itself was so beautiful with all of the tropical foliage and the wildlife. We saw chickens (of course), iguanas, lizards, and the property cats which were SO cute and sweet. There were 4 pools on the property and they are open 24 hours which we really loved! The staff was very friendly and accommodating. A small breakfast is served in the mornings, I really enjoyed the fruit and my husband loved the croissants. Something we didn't realize was we could've rented bikes for a day for free and we could have gotten a free breakfast cocktail. Definitely take advantage of that if you are staying!
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Rachel C.

Yelp
Stayed in SC6 - wonderful experience! Staff is so friendly & accommodating. Didn't meet any staff that didn't want to assist us right away. The breakfast was perfect for us to start our day with each day. Very quaint & quiet grounds but still a block from Duval Street. Couldn't have picked a better location! We walked to everything. The only thing I would suggest to the hotel is to add a mirror to the room. There were two girls staying in the room so only having the one mirror in the bathroom to get ready was a little inconvenient. But nothing we couldn't work with! Again, perfect stay! Will recommend to all friends & family visiting Key West! Thanks & can't wait to come back!

Sheila L.

Yelp
Yes, yes, yes! Loved this place! The staff, the room, the location and breakfast def recommend
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Kym H.

Yelp
This place is gorgeous and in a perfect location! 4 private pools and we used them all! Light breakfast in the mornings with fresh fruits, bagels, toast, hard boiled eggs, fresh juices, yogurt, iced tea coffee. Delicious! There are some great restaurants , so many that we didn't get to them all! Oh well next time! We highly recommend these cottages. So quaint and very clean. We stayed in the double kings cottage. A couple of things to mention: both rooms are upstairs and so is the only bathroom. The plus is that each room has its own sink vanity, do the definitely thought things through! We loved it!! Beds were extremely comfortable and cool. The grounds are well kept and immaculate. Everyone there was very nice as well! We sat in our rocking chairs on the front porch every night. Please if you want to feel the like your in a slice of heaven stay here!!

James B.

Yelp
This place is wonderful! We stayed one night recently and could not be more pleased with the ambience and hospitality provided. Every staff member we encountered was extremely friendly and hospitable. At check-in, Rachel gave us a tour of the property and explained the history of this hotel (it was originally a cigar factory). The grounds are beautiful, as was our room. Although our room was directly situated on busy Simonton Street, there was no noise disturbance inside. The room had a sitting area with a television (and cable service) and a separate bedroom with a very comfortable queen size bed. The room was well-appointed and the bath had a generous supply of upgraded toiletries. There are four swimming pools, one with a black surface which helps keep the water almost bath temperature. The grounds are beautifully landscaped with natural Florida foliage and flowers. A most delicious breakfast was served in a quiet corner of the property. Choices included French toast, Belgian waffles, fresh fruit, assorted pastries and breads, as well as coffee and juices. My wife and I highly recommend Simonton Court - we will be back again!
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Brenda P.

Yelp
At first, the inn seemed like just another tiny old home on Simonton: simple and nondescript. After briefly checking in, we opened the gate to go find our cottage. Wow! I was not ready for what followed; a bougainvillea framed path with private cottage entrances on either side. I discovered a whole new world hidden in there! Some even had their own private pool and sun deck areas. Our cottage was all the way towards the back and up a flight of stairs (naturally, no elevator). It was small, but it was also full of charm. The large verandah faced Simonton, but it had enough strategically placed landscaping to still give us plenty of privacy. Service was prompt and nonintrusive; our room was always made up and we had plenty of towels. Our privacy was kept at all times. From the website, I am guessing our room was the Orchid Mansion. Oh, one more thing, that was 2000 and most definitively pre-Yelp. Last weekend, 14 years later, I returned. It was as if I never left: exactly as it had been my first time. Simonton Courts is definitively kept up with lots of TLC. This time, our room was the Iris Cottage 2. It has two rooms, two bathrooms, living room and a little kitchenette area. Perfect! This particular cottage shared a private pool with just another cottage across the way. My only criticism is this: please add some blackout blinds to the master suite in C2! It's way too bright in the morning! The location cannot be any better. It is a short stroll to most of the sought after Key West locations. By walking through the adjacent (safe) alley, you are on Duval, right on Fat Tuesday's steps. From there, the world is yours. If you head south, you will find the quieter side of Duval with restaurants, wine and jazz bars. Head north and well, it can be the point of no return. Bar hopping, loud music, bachelor parties, and spring breaker types. It all depends on what kind of fun you are looking for I guess. The inn gate remains open throughout the day. At night, there is a code to get back in. This can be dangerous depending on where you end up at night. Make sure to write that code somewhere safe. Ha! There is street parking available as well as a private lot. Simonton Court is a little rustic. By that I mean, it's not shiny and new. You can tell it's been there for a while and that's exactly what I love about it. If you are looking for a chain hotel look and feel, go elsewhere. If you want authentic Key West charm and poise- this is it!
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Bridget G.

Yelp
So highly recommended! I would LOVE to stay here again. A friend and I went on a little overnight girls' trip to Key West. We were coming in on a tour bus and called ahead to ask if our room would be ready, and the staff kindly told us that if it wasn't, they could hold our luggage for us. We arrived just after 11AM and our room was ready! We stayed on the second floor of one of the larger buildings on the back of the property. The property is lush, green, secluded, and feels like paradise. We had to do lots of faux-model photoshoots! There are 4 pools around the complex that we were free to use, although only one was out in the open.... the smaller pools were between private bungalows and would have felt weird to use. Unfortunately, the weather kept us from using them at all. Our room was beautiful, clean, and with a big, comfortable four-post bed. There was a mini-fridge and a fully stocked bathroom, although it was a little weird that the shower didn't have a door or curtain, and one had to walk through the restroom in order to get to the patio. We would yell, "I'm coming through! I'm not looking!" as we walked through the bathroom if the other one was showering. The best part was the gorgeous private patio overlooking the pool/common area. We spent a lot of time hanging out there with wine, and I was so comfortable that I even fell asleep on the sofa. Comfortable, not drunk. Wanted to clarify. We loved it so much and didn't want to leave. We didn't even really mind spending a lot of time in our room. It was walkable to everything, and just near Front St. with all of the restaurants and bars. The only reason I'm not doing 5 stars is the bathroom privacy issue, and the complimentary buffet was OK, but not great. We were hoping for a little more; they served pre-frozen toaster waffles and pancakes, hard-boiled eggs, pastries, fruits, and that was about it. The cuuuuute grapefruit-shaped grapefruit holders were really exciting, though. I would be so excited to stay here again!
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Grace Q.

Yelp
This place is a gem! The location is perfect. Quiet place but close to the action of Key West. Accommodations were clean, quaint, yet up to date. The property is private and offers cottages and different types of rooms. Staying in the main house does require going up stairs. Breakfast is very good and included in the price with good variety. Loved this place and would love to return. Staff was also very nice, especially Paula and Beth. It's a home away from home.
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Elizabeth D.

Yelp
This is our new favorite place to stay in Key West! It's so charming and cozy. Each cottage is a little different from the others. Very private. The decor is beautiful! Comfortable bed, sofa and chairs. Refrigerator, microwave, utensils, iron, ironing board, writing desk and hair dryer in each room. Some of the cottages have a private pool and others have an indoor bar, depending on how many people you are with, there is a cottage for everyone! I highly recommend this place! We will be staying here again next year.
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Lynsey H.

Yelp
My husband and I stayed at Simonton Court this week for 3 nights whilst vacationing in Key West. What a winner! The mansion house, cottages and grounds are very lush, quaint and relaxing. The man who helped us check-in was very welcoming and friendly and carried our case all the way to our room. He was also able to advise us on nearby free parking for during our stay. Accommodation: Our room was on the top floor of the mansion house, we had a huge bed, seating area and small balcony. We loved it, the only negative was that you are on the road, so at times it was a bit noisy. Apart from that it was great, the bed was very comfortable and we slept great. I wasn't sure about the shower at first as it seemed a bit outdated, but it was powerful and sufficient. For ladies, they don't provide conditioner, only shampoo and shower gel in a dispenser. Grounds: There are 4 pools, 1 main pool and 3 smaller pools by the cottages. It was always empty around the pool, so you could get your pick of lounger and relax. We did think the pools had a high chlorine content and it stung our skin a bit. We had to shower immediately after getting out as the smell was strong and our eyes were red and sore. Breakfast: We didn't have high expectations for breakfast, but we were wrong and were really impressed with the selection available. The usual juices and hot drinks, plus bagels, French toast, waffles, grapefruit and bananas, hard boiled eggs and yogurts. Full variety of condiments as well. You can definitely make something of it to suit your taste. The staff at breakfast really went out of the way to help us and bring everything to us at our table. They were very friendly. Location: The Inn is minutes away from Duval St (the main drag) and everything you may want to see in Key West is within walking distance. Overall, we had a great experience and relaxing stay here and would definitely stay here again if visiting Key West. The only reason it isn't getting a 5 star review is due to the pool chlorine and the noise from the road and nearby guest rooms. We did advise staff about the chlorine and they are going to look into it.
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Dave H.

Yelp
Beautiful collection of cottages, two (maybe 3?) pools (one spa beautiful, the other dated, another seemed to be connected to a different property), with gorgeous gardens packed with orchids, orchids on orchids, and a resident cat friendlier than most people. Adorable.

Andy B.

Yelp
In a world of soulless corporate hotels, this place is a welcome surprise. Really beautiful property tucked away just a block off Duval. Several buildings to choose from along with 6 or 8 beautiful cottages. Everything was great from check in to check out. Every employee I encountered was friendly and helpful. I will definitely stay again on my next trip to Key West. Highly recommended.
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Suzanne M.

Yelp
We headed here based on a recommandation from the owner of a small Inn in Marathon Key. She said whenever she heads to Key West without a reservation, she always comes here first to see if they have any available rooms. We were not only able to get a room, because we walked in, they dropped the price from $300-something to $140 for one of the second floor mansion rooms (MA-2). The gal at the front desk was reeeeeeally pleasant and helpful getting us set up with the room and guiding us to free parking options a couple short blocks away (they offer parking for $28ish). The room is gorgeous and the location is just a couple blocks from all of the action. There are four pools available to use, each one a little different set-up. She said that this used to be four different properties, each came with its own pool and the owner bought and merged the properties together. We took a swim tonight and the temp was perfect. It is a little creepy that there is a live web-cam of the pool area on their website, but no biggie. Very clean. Comfy bed. Free breakfast in the morning (i.e., bagels, breads, honey, cream cheese, peanut butter, fresh grapefruit, apples, oranges, yogurt, juice, coffee). Water cooler & ice tea are always out and available. Free wi-fi... read a bad review about that, but I haven't had an issue with it (uploaded pictures, watched a video, surfed around - no glitches, speed is fine). The shower is large (no tub in this room) and tiled. It's one that you walk in and there's no need for a curtain because it's big enough that the water doesn't go out. Hair dryer in the room, mini fridge, tv, iron, a/c. I love it! Unless there is a hidden elevator, I only saw stairs to get to these upper rooms, but there are lower level rooms on the property. We will definitely be back!
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Wayne K.

Yelp
My buddy had arranged staying here after looking at a few places where a group of 7 of us could all hangout together. This was a great location for us as it provided a really tranquil place where we could hangout in the evenings without enduring the drunkenness of Duval Street, while still being close to all the other fun places, like the beach, Hemmingway House, etc. The place had 4 swimming pools and the lush garden really made it feel tranquil and pleasant while we sat most nights drinking on the porch while talking and joking in the late hours. I also have to give props to this place due to the helpful staff and the friendly vibe all around...even by the other guests. There were a few downsides, which doesn't make me give it 5 stars. The Internet didn't always work, the free breakfast was very mediocre, and the furniture was pretty uncomfortable, but for the sheer tranquil atmosphere, this is a great spot to stay with a group of friends.
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Lori G.

Yelp
We have stayed at Simonton Court twice, and my sister and brother-in-law have stayed there at least four times, possibly more. We all love it, although don't get me wrong, it's pricey. The grounds consist of several small cottages and one large Victorian manor house, tucked into a lush tropical garden. The location is both secluded and in the heart of the action on lower Duval Street at the same time. It is also just a few blocks from the historic seaport. Many of the cottage rooms have private porches or decks, and at night, the staff comes through and lights small lamps on all the patio tables. It's very cozy. There is one large pool and 3 or 4 smaller pools dotting the property. Although guests can technically use any of the pools, you do tend to feel a little possessive of one of the smaller pools, especially if it is steps from your door. On our most recent trip, my husband and I were in the room adjacent to my sister and brother-in-law (Hibiscus and Royal Poinciana) and we spent a lot of time sipping drinks around the small heated pool right outside. The rooms are decorated in a comfortable, tropical style. They have retained many of the original features of the cottages, which were originally part of a cigar factory complex. My only complaint was that the bed was up in a loft, which we knew when we booked the room ( Bougainvillea). Although they had provided extra fans, the a/c never really reached up that high, and I was a little too warm. Also, it's no fun scrambling down to the bathroom in the middle of the night after you've been out carousing. We made sure to select a different room for next time. Each morning they serve a continental breakfast at the big pool. I've only gone once or twice, since personally, breakfast is my favorite meal and there are so many amazing places to dine. Why take up precious room in your stomach with a croissant, when there is Lobster Benedict awaiting? There is water and iced tea available by the pool all day. We love to stay at Simonton because the grounds are so lovely, quiet, and romantic, and the location is fantastic. We have tried several other inns and hotels, and this is by far our favorite. The cost might be prohibitive to some people, but we think you get what you pay for.
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Harry H.

Yelp
I highly recommend Simonton Court for many reasons. The staff is a adorable, always friendly, responsive. The breakfast in the morning is quite satisfying. The rooms are spacious and private. Perfect if you want to stay inside during hot weather. So why only give a 3? Wi-FI. Our room did not have wifi. Multiple devices could not connect to the network we were told to connect to because of a weak signal. We wouldn't have booked the room without wifi and when we complained we were told to go outside closer to the router hanging from the porch ceiling. Not acceptable. It's 2017. I had to upgrade my AT&T plan just to do work here. I had to use my phone as a personal hotspot. I won't likely return because of this one small issue. Otherwise, awesome place.
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Sam J.

Yelp
Stayed here a few weekends ago with my husband. Book the room nine days out from my stay. Our friend was having an impromptu wedding in Key West so not planning to go that weekend my husband and I needed to find something affordable for one night. With such late notice there wasn't much in our price range. When I called Simonton Court the lady I spoke with was extremely helpful! She even went online to see what the online websites like trivago were doing for pricing and ended up beating all of the prices for me. Our friends were staying at the pier house which was in walking distance. We had a cute little cottage right off of the street. The cottage had a little fitting room area and then a door to the master and bathroom. They had many pools to choose from if we had time to swim, and had a nice complementary breakfast poolside, the next morning before we left. The staff was very friendly and inviting. Would definitely stay here again!
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Mareni S.

Yelp
Always a wonderful experience. Very convenient location. Friendly, helpful staff. Complimentary breakfast. $25.00 parking per day on the premises.
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Joanna S.

Yelp
Wow I just read some online reviews for the week of August 8th to 13th and I have no idea what people's issues are. Maybe they have never stayed in Key West. The Simonton is by far the best "key west" cottage and inn in the area. We were there with a group of 9 all staying in different locations. MA, CO and SC and guess what we all loved it. The pools are great and the big one was really nice. Breakfast was first class. They brought your food too you. I can not begin to praise them enough. I come to key west with my sister because its her favorite town. But now after staying at the Simonton its a favorite of mine. Its vintage, rustic but clean, comfortable with top notch amenities.
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Bryan S.

Yelp
Do yourself a favor and stay here. So many pros and no cons. First off, it is beautiful. I mean BEAUTIFUL. It is also historic. In the heart of Key West. No Ubers or vehicles needed. I was here for a wedding and I never got into a car the entire weekend. This place is worth the price tag. The only negative was that I was unable to shag one of the bridesmaids (not the hotels fault).
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Kristi S.

Yelp
I absolutely loved our stay here this weekend. We had a small cottage with a porch. This place is very quaint and well located in Key West- a block off Duval street. There are many pools on the property. All of the units look really cute and I loved walking through the greenery on the property. I would stay here again.
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Juliane V.

Yelp
The lady up front was really rude! She say we can cancel our hotel reservation like she don't care. Really bad customer service and we will not be back! Definitely not recommend this place.
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Q D.

Yelp
Rude rude rude!!! The lady was really rude to me. How someone going to say I haven't got the money from your booking yet so you can cancel your hotel reservations? Like really? I'm never coming back here and don't recommend this place!

Lori B.

Yelp
Well I'm sorry to say, this place has become shabby. Toothpaste on the framed artwork in the bathroom. Someone left there fingernail clippings on the end table. Guess the maids don't really clean well. Things are old and used. The pillows on our sofa need replaced. They're just dirty from use. Not reinventing any money in the place. Won't be back. Also, the maid swept the bathroom floor onto the sisal rug and never vacuumed it up. Gross
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Steve Y.

Yelp
This is the best place we've stayed at while visiting Key West and we will never stay anyplace else on our future visits! Simonton Court is a charming oasis at the perfect location in the heart of Key West and just a block away from world famous Duval Street. The beautiful rooms and cottages are situated on very well kept grounds filled with tropical foliage and the super friendly staff here is second to none. Such a wonderful experience, we highly recommend!
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Alexander J.

Yelp
The staff here are amazing; very friendly and helpful. This property is basically a jewel for a Key West B and B. The only down sides are somewhat minor, but worth noting: a) bathrooms are a little dated with marginal water pressure; b) not many outlets for charging phones and computers: could use a power strip as a fix; c) breakfast is a nice touch but the reality was when I was there they only offered a bagel or toast or a hard boiled egg. And yogurt. All of these things are minor but would enhance the stay if they were ever to act on them. One thing that I did not consider minor: they have multiple security cameras that regularly rotate and tilt down on guests which feels a little unnerving like you're always being watched. On a vacation, this is not a welcomed feeling. It made me wonder why they needed those cameras. Did they have problems in the past that warranted such aggressive cameras? It was a little unnerving. Felt like I was the subject of a reality tv show. It would be nice to lay out at the pool in quiet without feeling like you're being watched. Regardless of these notes, I would return here. Among the good things: the place has character; 3 small pools; Set off from the street so it's like walking into a semi-private retreat; the location is only a few blocks from Duval and the marina (great location); plenty of towels made available for room and pool; iced tea is available 24/7 in the common area near the main pool is a nice touch; everything is kept clean; as previously stated, an excellent staff.
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Katie D.

Yelp
Stayed here a couple of times. This time we scouted out new hotels for the next visit though. It's just too expensive for what you get. I love the tranquil setting and its convenient location, and the main pool is usually warm and lovely, but everything else is a let down. The smaller pools are usually cold and a little dirty. The rooms are not super clean and the bathrooms are in dire need of updating. (Saw two roaches in the bathroom this time.) There is nothing on the breakfast bar that I would eat (but I'm picky). The staff is friendly and helpful unless they're busy with something more important. Oh, and three guests were visited by a cat burglar in the middle of the night during the last stay. Apparently, it's not the first time either.